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Synthesis of the chromophores of fluorescent proteins and their analogs

Russian Journal of Bioorganic Chemistry volume 39, pages 223–244 (2013)Cite this article

Abstract

Members of the green fluorescent protein (GFP) family are widely used in experimental biology as genetically encoded fluorescent tags. Chromophores of GFP-like proteins share a common structural core: 3,5-dihydro-4H-imidazol-4-one. This review covers synthetic approaches to 3,5-dihydro-4H-imida-zol-4-ones, substituted at different positions. General, as well as specific methods, represented by single examples are considered. The most popular synthetic route to substituted 3,5-dihydro-4H-imidazol-4-ones includes synthesis of azlactones, followed by transformation into N-acyldehydroamino acids and, finally, cyclization into target heterocycles. Accordingly, the review is divided into three parts: the first part covers syntheses of azlactones, the second part covers main approaches to N-acyldehydroamino acids, and in the third part we summarize cyclizations of N-acyldehydroamino acids, as well as all other approaches to 3,5-dihydro-4H-imidazol-4-ones.

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Abbreviations

Ar:

aryl

CDI:

carbonyldiimidazole

DABCO:

1,4-diazabicyclo[2,2,2]octane

DBU:

diazabicycloundecene

DDQ:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

diethyl azodicarboxylate

imidazolone:

5-arylene-3,5-dihydro-4H-imi-dazole-4-one

DIPEA:

diisopropylethylamine

GFP:

green flu-orescent protein

HOBt:

1-hydroxybenzotriazole

LDA:

lithium diisopropylamide

MS:

molecular sieves

oxazolone:

5-arylidene-3,5-dihydro-4H-oxazol-4-one

NBS:

N-bromosuccineimide

PMB:

p-methoxybenzyl

Py:

pyridine

TBDMS:

tert-butyldime-thylsilyl

Ts:

tosyl

FP:

fluorescent protein

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Makalya 16/10, Moscow, 117997, Russia

    M. S. Baranov, K. A. Lukyanov & I. V. Yampolsky

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  1. M. S. Baranov
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  2. K. A. Lukyanov
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  3. I. V. Yampolsky
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Original Russian Text © M.S. Baranov, K.A. Lukyanov, I.V. Yampolsky, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 3, pp. 255–276.

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Baranov, M.S., Lukyanov, K.A. & Yampolsky, I.V. Synthesis of the chromophores of fluorescent proteins and their analogs. Russ J Bioorg Chem 39, 223–244 (2013). https://doi.org/10.1134/S1068162013030047

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Keywords

  • fluorescent protein
  • chromophore
  • GFP
  • azlactone
  • imidazolone